To Work or Not to Work?

That is the question that is plaguing my tiny but very relaxed brain of late. Actually that question popped up most prominently in May of this year when I felt extremely restless and simultaneously guilt-ridden about taking time off to smell the roses. I was brought up to believe that I should work until I die, or so several of my “fortune tellers” have told me in my 20’s when I paid them a lot of money to tell me what the rest of my life will hold. A side digression – how come none of the fortune tellers knew my name if they could tell fortunes??? Suffice to say I stopped handing my hard-earned money to these soothsayers long ago and charted my own future by not working for over a year now. I have NO regrets whatsoever about taking time off to reconnect with people; to learn about them as true human beings instead of business prospects; and most of all, to rediscover what I really enjoy in life. This will be the one period of my life where I will always remember in full technic color and in minute details of the things I experienced and time spent with friends and family.

But let’s be honest, if I live to 100, I can’t live off Uncle Sam’s measly social security check; nor will I have enough savings if I continue to travel or dine the way I have been doing so unless I move to a hut (the downside of Wall Street is that it instills in one a terrible habit of wanting to live it up). Common sense so far dictates to me that I only travel high end once every few months, during my downtime I eat $.99 per pack instant noodles or leftovers, and sponge off my friends for lodging in cities where I have friends.

The question now I am confronted with isn’t so much to work or not to work, but rather what kind of work should I do in the next chapter of my life? Isn’t it remarkable that after a year off I actually fear that I have no skills other than being able to tell someone what stock to buy or sell (though that isn’t exactly a skill in today’s market environment)?

My choices:
1) Continue to travel until I run out of money (within my control, but by then will I have any skills left for any job?)
2) Go back to the Street or somewhere in the finance arena, either do the same thing I did or work for a client (Not within my control, it will be market driven)
3) Go do something else completely different – like writing – one of my passions (within my control but will I get published?)
4) Start my own business (within my control, though I am utterly clueless as to what business)
5) Keep buying my weekly Lotto ticket and hope I will win and truly retire (Not within my control, up to a higher deity)

Good thing that at least #1,3 and 4 are within my control. So I guess that should help me decide what to do next? Stay tuned, when I finally grow up I will let you know what my next chapter will look like…….